期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 38, 页码 11173-11176出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505898
关键词
asymmetric catalysis; peptides; phosphothreonine; quinoline; transfer hydrogenation
资金
- National Institutes of Health [NIH R01-GM096403]
- National Science Foundation Graduate Research Fellowship Program
Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA-catalyzed reductions were carried out. pThr-containing peptides lead to the observation of enantio-selectivities of up to 94:6 e.r. with 2-substituted quinolines containing C8-amino functionality. NMR studies indicate that hydrogen-bonding interactions promote strong complexation between substrates and a rigid beta-turn catalyst.
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